tagTranssexuals & CrossdressersA Weekend Together Ch. 01

A Weekend Together Ch. 01


My fiancée and I, decide one weekend to indulge in my fetish of cross-dressing. We rented a hotel room down town across the street from the local gay club for Friday and Saturday night. I checked in when I got off work Friday afternoon upon entering the room I stripped of my male clothes and put them away in my suitcase. The plan was I was going to spend the whole weekend as a girl.

I got my razor and shaving cream out and went to the bathroom. I shaved every bit of body hair I had, which wasn't much considering I keep it shaved regularly. Just as I was finishing up Jessica knocked on the door. I wrapped a towel around myself and opened the door. She came in carrying shopping bags and a big smile on her face. She told me she had picked up some things this morning because she was tired of seeing me in the same old clothes.

She saw that I had just got done shaving and asked if I was ready to start getting dressed. I told her no I needed to take a shower first. She said, "well hurry up, I'm ready to see my girl friend."

I laughed at this as did she, and asked her to walk down and get my wig out of the car. It was brand new and I hadn't even gotten to wear it yet and I didn't want to mess it up by packing it in my suitcase. She said she wouldn't mind doing that for me at all so I grabbed my feminine body wash and took off to the shower.

I took my time enjoying the feel of the hot water splashing over my hairless body. I guess I took too long because by the time I was out and dry Jessica had already dressed. She had chosen a very low cut lime green halter-top, her blue j-lo miniskirt, my favorite, and some sexy spiked heels. She didn't need any makeup, she was perfect just the way she was.

Her face lit up as she watched me enter the room, she just stared for a minute before saying first things first. She opened her tote bag and pulled out the little pink cock cage I had purchased for myself right before we started our relationship. She unlocked it, keeping the key she handed it to me saying, "You're my girl until I say differently now put that on and lock it."

I did as I was told as she pull a necklace out of her bag and strung it through the key and fastened it around her neck. I had to really concentrate very hard to keep myself from getting hard. Finally I snapped the lock closed and I was her captive, her holding the only key meant I had no chance of escape. She walked over with a grin on her face and kissed me as she let her hand slide down to stroke my balls. I moaned in discomfort as my cock tried to grow in its cage. She laughed and said, "What is it baby? Don't like being teased?"

With an evil grin she turned around and pulled up the back of her skirt showing her green lacy thong panties. She looked back at me as she pushed herself against me. She bent over as she started rubbing herself against my caged cock, teasing me. She continued this for a few minutes and just as I moved to grab her hips she pulled away. She said, "enough playing for now."

She waked over to my suitcase and pulled out my breast forms and the adhesive that attaches them to my skin, normally I don't use it. I asked her why I had to glue them on instead of just wearing a bra, like usual. Her response was, "because your dress doesn't allow you to wear a bra."

I nodded not knowing which dress she had in mind. She helped me apply the breasts so they were straight and in the correct position. Then she pulled out a pair of black lace top fishnet stockings and handed them to me. I sat on the edge of the bad and slowly rolled them up my legs as she ruffled through one of her shopping bags. I stood back up as I straightened the tops, as I finished she said, "Ok, here is what's next."

She held out a pink butt plug and a tube of lube, I was shocked by this and a little skeptical as I took it from her. I applied the lube to the end of the plug and bent over the bed. I began to slowly work it inside of myself as she stood there watching intently. After a few minutes I guess she got impatient with my playing and said "hurry up we don't have all night."

With that I pushed it the rest of the way in and stood up again as the through a pink satin thong at me. I looked at her and asked about my special panties that hid my male parts. She said I didn't need it nobody was going to notice it and it wasn't going to grow anyway. Reluctantly I bent down and stepped into the panties pulling them up my legs. They were a size to small, which made them hug me very tight and held the plug as deep as it could go.

Then she pulled out a pink halter dress from another of her bags. She handed it to me and I looked it over, it looked like it was going to be too small. I held it out and stepped into it, I pulled it up and she came over to tie the neck for me. Once she had it tied I looked in the mirror and saw how short it really was. In the back it stopped right at the crease between my legs and ass. I looked at her in shock and said, "I can't wear this, if I bend over even a tiny bit everyone will be able to see everything."

She laughed and said, "o it will be fine just don't bend over."

This didn't sound reassuring at all but before I could really argue she grabbed my arm and sat me down on the bed. She began to apply my make up; she applied foundation, pink eye shadow, and black eye liner. She did it just the way I like it enough to make me look like a girl but not too I looked like a whore. Then she handed me a tube of pink lip-gloss and I applied it as she grabbed my new wig. She helped me put it on then fasten it with a few bobby pins. I was ecstatic with how natural it looked, but it better be as much as I spent on it.

Then she pulled out nail polish and painted my normally long nails the same pink color as my dress. When she was done she declared I was officially a women, which sent us both into a pit of laughter. I got up and walked over to the mirror and as always I was amazed at the transformation. I sat there and posed in front of it for a few minutes before I heard her say, "ok get your shoes on, its time to go"

I put on a pair of strappy little three-inch heels, we decided the stripper heels were too much for the night and we were on our way. It was about 10 o'clock when we entered the club and they were already pretty busy. We made our way straight to the bar and were ordering drinks. I didn't even realize I was bent over a little until I felt a hand touch my bare ass.

I jumped turning around to see a pretty good-looking guy. He said his name was josh and we were two very pretty ladies and that he just wanted to introduce himself and buy us a drink. I smiled and thanked him telling him my name was Ashley and this was Jessica. He said he would be around a while if we wanted to talk a little bit and get to know one another. I told him we would find him a little later, we thanked him again or the drinks and walked around to mingle through the people.

We got hit on and approached a few more times but no one that really got our attention. Then while we were dancing together I saw him, he was at the bar looking right at me. He was tall with brown hair and a very muscular body, he smiled at me and I smiled back, then he started walking towards us. He grabbed me pulling me against his firm chest and I was on cloud nine as he put his mouth to my ear and said, "You are one of the most beautiful girls I have ever seen my name is Ben and I would love to take you home tonight."

I smiled and replied, "thank you very much I'm Ashley and this is my fiancée Jessica."

He looked discouraged as he started to release me I asked him to hold on just a second. I pulled away and told Jessica what he said and her eyes lit up and she said, "you know I have always wanted to watch so it's totally up to you. All I'm saying is he is hot."

I turned back to him and asked if he had a pen and something to write on. He pulled a pen out of his pocket and handed me a napkin. I wrote down my name, phone number and the room number we were staying in. I handed it to him and told him, "We are in the hotel across the street. Jessica just wants to sit in the corner and watch. Meet us there at midnight."

He smiled and said he'd be there. He wrapped his arms around my waist and put his mouth to mine kissing me deeply, and then he released me and walked away. I turned back to Jessica and she was falling over in laughter. We danced and had a few more drinks till about eleven thirty. And we decided it was time to head back to the room for my date. As soon as we were in the door she grabbed me and started kissing me. She told me she was so excited her panties were soaked and probably dripping.

She walked over to her bag and pulled out the rabbit vibrator I bought her for Christmas and set it on the table in the corner then she pulled a condom out and set it on the bed with the lube. She said I should take out my plug so it doesn't get in the way, so I went into the bathroom and pulled my panties down and took it out feeling the emptiness inside as I laid it in the sink. I sat down too pee with my panties around my ankles and Jessica walked in to check on me. She instantly began laughing and said, "that makes you act more like a girl then I thought. You have to sit to pee so you don't make a mess and you have to wipe.

I laughed realizing she was completely right as I wiped and pulled my panties back up. She kissed me deeply again and telling me she loved me and she couldn't wait to see me with a man. She reapplied my lip-gloss saying he would be here any minute. As soon as we walked back into the room and sat down on the bed there was a knock at the door. We both jumped up, she walked over to sit in her corner and I went and opened the door.

It was Ben of course, I opened the door and invited him in and as soon as the door was closed he grabbed me around the waist and pulled me tight against his hard body. He pressed his lips to mine and we stood there kissing. My hands were wrapped around his neck as his hands ran all over my back and down to my ass. We inched our way over to the foot of the bed and I pulled his shirt off exposing his perfectly chiseled chest and stomach. I couldn't help but run my hands over it. He reached behind my neck and untied my dress.

I pushed him down on the bed into a sitting position and pushed my dress to the floor. Climbing on top of him I wrapped my arms back around his neck and returned my lips to his and kissed him as he ran his hands all over my bareback ass and legs.

I felt the bulge in his pants under me and couldn't contain myself anymore, I had to see it and taste it. I broke the kiss and slid down to my knees on the floor I looked up into his eyes as I started to undo his pants. He was looking at the corner and as I looked Jessica's panties were on the table and her hand was up her skirt.

I smiled to myself as I turned back and pulled his zipper down. I grabbed his waistband and he lifted himself up with his arms allowing me to pull them down. His cock was about eight inches long and not to thick, it was perfect in my book. After staring in awe for a minute I finished taking his pants off and leaving them on the floor.

I moved my mouth to his cock and lightly kissed the head. Then I stuck out my tongue and swirled it around just the head. I ran my tongue down the underside and back up. I swirled my tongue all around his shaft licking every bit of it then I moved my mouth down to his balls where I licked each one and then individually sucked them for a few minutes. Then I ran my tongue back up his cock and wrapped my lips around the head. I slowly slid my mouth down his shaft making sure he could feel my tongue ring on the underside as I did. I began to move my head up and down the length of his cock. After a few minutes he stopped me saying, "damn baby if you don't stop I'm going to cum."

I smiled at this and stood up and kissed him before walking over to the nightstand and grabbed the condom and lube. I set the lube down on the bed beside him and got back down on my knees between his legs. I opened the condom package and rolled it onto his rock hard cock. He stood and helped me up kissing me again as he did. He then moved me towards the bed and bent me over it. Grabbing the waistband of my panties I looked back at him and smiled as he slowly pulled them down my nylon covered legs to my ankles. He then picked up the lube and squirted it onto two of his fingers and slowly began pressing them against my tight little hole causing me to moan, thanks to the plug I had been wearing there was no resistance at all. He began moving them in and out of me making me moan loader with each stroke he went a little deeper and a little faster.

After a few minutes he decided he had me loosened up enough and pulled his fingers out leaving me feeling empty for a minute. He moved to the side of me as he applied some lube to the head of his cock and asked if I wanted to spread it for him. I smiled innocently as I moved my hand to his cock and slowly spread the lube over the head with my finger. This caused him to groan and pull away he positioned himself behind me and I moaned as I felt his cock head make contact with my hole. I pushed back against it just a little and said, "o yes I want your big cock please give it to me now."

Hearing that he needed no more coercion and slowly began to push inside me as another moan escaped my lips. Then before I knew it he was all the way in and I felt his hips pressed against my ass. He stayed still for a moment as we both were over come with great pleasure from him being deep inside me. Then he slowly started to pull out as I groaned in disappointment only to feel him thrust right back feeling his balls lightly slap against me as I gasped. He moved his hand to my hips and held me tightly as he pulled out till just the head was inside again. I moaned as I tried to push back on his cock again but his grip was too strong. I looked back and said "please fuck me baby I need it so bad, I'm falling in love with your cock inside me."

With that he slowly pushed back inside me as he groaned. He began to get a rhythm going slow at first but gaining speed with each thrust. He grabbed my right leg lifting it up so my foot was planted on the bed giving him better access to my tight ass as he began fucking me harder. I cried out in complete pleasure with each thrust as he was going even deeper then before.

As he continued fucking me I looked over at Jessica. She now had her skirt around her waist and her legs spread wide over the arms of the chair, as she rubbed her clit furiously, she was pounding herself with her vibrator, continued to watch her live show. As I was paying attention to Jessica I was shocked as he moved his hand to the back of my neck and sliding his fingers around the front of my throat he pulled me up so his chest was against my back. With his cock still moving deep inside me he turned my head and began kissing me as his hands moved to my chest and began feeling on my fake tits. Then he began kissing and nibbling my neck as he turned around and wrapped his arms tightly around me so his cock didn't lose contact with my hole as he slowly sat down on the bed with me backwards on top of him.

He laid back on the bed letting his hands move to my hips again as he watched me start moving my ass up and down on his hard cock. I slid all the way up so just the head was inside me as I reached down between his legs and began massaging his balls. This made him moan as he roughly tightened his grip on my hips and roughly pulled me back down on his cock. I continued to play with his balls as I rode him as he controlled my speed by my hips. Then I picked my feet up so they were flat on the bed and I lay back against him lifting my weight off him. He took the hint and began thrusting into me again as I moaned he reached around me and I felt him run his hands all over my tits and stomach then to my caged clit. After running his fingers all over it he brought his fingers to my mouth coved in my precum that was leaking like a fountain and I licked them clean.

After a few minutes of licking and sucking my precum off his fingers I got up and turned around facing him as I climbed back on top of him. As I sat down on him His cock slid right back inside my ass with no assistance. I began moving up and down on his cock enjoying the feeling of it then I sat all the way down feeling him deep inside me. I sat the enjoying it for a moment then began to grind myself on his cock just the way Jessica did to me that I enjoyed so much. This got the desired affect as he began to shiver and groan and buck his hips as he grabbed at my waist. I rode his cock like a pro and I could tell he was getting close to blowing his load.

He pulled me to him and kissed me deeply as he wrapped his arms tightly around me and rolled us over, before I knew what was happening I was on my back. I wrapped my legs around him locking my ankles together as he started fucking me even harder. He looked at me saying he was about to cum and I moaned begging him to. Continued to moan as he fucked me hard and all of a sudden he thrust deep inside me he grunted and I felt his cock expand and spasm as it exploded inside me. He looked into my eyes then kissed me as his cock slowly began to shrink.

We lay there for a few minutes catching our breath before he slowly pulled his limp cock out of me and kissed me again. Then excused himself to the bathroom to clean up. I got up and took off the heels and thigh highs, then put on a purple sating spaghetti strap nighty Jessica had pulled out for me earlier and matching string bikini panties.

He came out of the bathroom saying that was amazing and how he never had sex that good in his life. Then asked if he could take us to dinner the fallowing night I looked to Jessica and she nodded her head in approval. I smiled telling him yes and to call us tomorrow to let us know where and what time. I showed him to the door where he gave me a long passionate goodnight kiss and another squeeze of my ass before he left.

I closed and locked the door behind him and turned and leaned back against the door as I sighed in bliss. As I looked back at the room I saw Jessica on her back on the bed totally naked with her legs spread wide. I walked over and climbed on the bed on hands and knees knowing what she wanted. I started kissing her left knee and leaving a trail of kisses all the way down her inner thigh stopping as I felt the hairless lip of her pussy. Then I repeated the actions on the right leg but I didn't stop when I got to her lip though. I kissed her pussy dead on and her clit, which caused her to shiver and moan a little. she was extremely wet as I began moving my tongue from the top of her slit to the bottom. I sucked and slurped at her pussy eating all her cum I could get that had accumulated during her show. Then I moved my tongue to her clit and slowly began massaging it and nibbling it a little. This made her go wild and she reached down grabbing my hair pulled me tightly against her and I continued my assault on her clit until she moaned and I felt her body convulse in orgasm.

I crawled up on top of her and kissed her as she grabbed my ass through my panties the crotch already soaked with my precum. I looked at her and said, "Will you please unlock the cage so I can make love to you and how much I enjoyed being able to put on that show for you."

She refused saying, "no I'm not unlocking it for any reason you are my girl for the weekend and girls don't have cocks. It's time to go to sleep"

With that she pushed me off her getting up she put on a nighty and matching panties identical to mine but in red. Then climbing into bed she snuggled up to my back cradling me and we went to sleep as two girls in love.

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